7,7-dicyanobenzoquinone methide | 83928-83-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7,7-dicyanobenzoquinone methide
• 英文别名: 2-(4-Oxo-2,5-cyclohexadien-1-ylidene)malononitrile；2-(4-oxocyclohexa-2,5-dien-1-ylidene)propanedinitrile
• CAS: 83928-83-0
• 化学式: C₉H₄N₂O
• 分子量: 156.144
• InChiKey: DDKAAPHFDXZGCJ-UHFFFAOYSA-N

物化性质

• 熔点：
  147 °C(Solv: ethanol (64-17-5))
• 沸点：
  282.0±40.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7,7-dicyanobenzoquinone methide 在 氢化钾 、 四氯化钛 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  New electron acceptors: synthesis, electrochemistry, and radical anions of N,7,7-tricyanoquinomethanimines and x-ray crystal structures of the trimethyl and tetramethyl derivatives

  摘要：

  The reaction of a range of quinones 3 with malononitrile in the presence of titanium tetrachloride/pyridine yields dicyanoquinomethides 4, which on reaction with N,N'-bis(trimethylsilyl)carbodiimide are converted into the corresponding N,7,7-tricyanoquinomethanimines 6. The solution electrochemical redox properties of compounds 6 have been studied by cyclic voltammetry; they are strong acceptors which readily form radical anions and dianions. The radical anions of N,7,7-tricyanoquinodimethanimine 6a and the tetra-, tri- and dimethyl derivatives 6c, 6d, and 6e, respectively, have been studied by ESR and ENDOR spectroscopy. X-ray crystal structure analysis reveals that trimethyl derivative 6d is planar, whereas the tetramethyl derivative 6c is strongly deformed with the ring existing in a boat conformation, similar to that found previously for tetrasubstituted TCNQ derivatives.

  DOI：

  10.1021/jo00032a017
• 作为产物：
  描述：

  2-(4-oxocyclohexylidene)malononitrile 在 manganese(IV) oxide 、 3 A molecular sieve 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以45%的产率得到7,7-dicyanobenzoquinone methide
  参考文献：
  名称：

  Convenient monoketalization of 1,4-cyclohexanedione. Synthesis of new quinone methides

  摘要：

  DOI：

  10.1021/jo00149a028

文献信息

• Preparation of Novel Electron-Accepting Quinone Methide Imines and Their Polymerizations
  作者：Shouji Iwatsuki、Takahito Itoh、Hiromu Itoh

  DOI：10.1246/cl.1988.1187

  日期：1988.7.5

  N,7,7-Tricyanoquinone methide imine (1), N,11,11-tricyano-1,4-naphthoquinone methide imine (2), and N,15,15-tricyano-9,10-anthraquinone methide imine (3) were successfully prepared as novel electron-accepting quinone methide imine compounds. 1 is homopolymerizable with free radical and anionic initiators, while 2 and 3 are not.

  N,7,7-三氰基醌甲基亚胺 (1)、N,11,11-三氰基-1,4-萘醌甲基亚胺 (2) 和 N,15,15-三氰基-9,10-蒽醌甲基亚胺 (3) ) 被成功制备为新型的受电子醌甲基亚胺化合物。1 可与自由基和阴离子引发剂均聚，而 2 和 3 则不能。
• HYATT, J. A., J. ORG. CHEM., 1983, 48, N 1, 129-131
  作者：HYATT, J. A.

  DOI：——

  日期：——
• Spontaneous Polymerization Mechanism of 7,7-Dicyanobenzoquinone Methide with <i>p</i>-Methoxystyrene
  作者：Yukihiro Mitsuda、Shuji Kawaguchi、Takahiro Uno、Masataka Kubo、Takahito Itoh

  DOI：10.1021/ma0352429

  日期：2004.2.1

  Spontaneous polymerization of 7,7-dicyanobenzoquinone methide (CQM) with p-methoxystyrene (MeOSt) was investigated. An alternating copolymer of CQM with MeOSt was obtained as the hexane-insoluble product, and a small amount of a 1:2 cycloadduct of CQM:MeOSt in addition to large amounts of unreacted CQM and MeOSt was obtained as the hexane-soluble product. To clarify an active intermediate in this reaction, spontaneous polymerizations of CQM with MeOSt were carried out in the presence of additives such as 2,2,6,6-tetramethylpiperidine-1-oxy (TEMPO) and acetic acid and in three solvents with different polarity. The spontaneous reaction in the presence of the TEMPO did not afford any products trapped by TEMPO. On the other hand, the reaction in the presence of acetic acid gave a 1:1:1 adduct of CQM:MeOSt: acetic acid in a quantitative yield. It was concluded from these results that the spontaneous polymerization of CQM with MeOSt might proceed via a zwitterionic intermediate, which has gauche and trans forms.
• COLORING COMPOSITION, LIGHT ABSORPTION ANISOTROPIC FILM, LAMINATE, AND IMAGE DISPLAY DEVICE
  申请人：FUJIFILM Corporation

  公开号：US20190101676A1

  公开（公告）日：2019-04-04

  An object of the invention is to provide a coloring composition with which a light absorption anisotropic film having excellent light resistance can be formed, a light absorption anisotropic film, a laminate, and an image display device. A coloring composition according to the invention contains a dichroic dye compound having an azo group; and an oxidant or a singlet oxygen quencher.
• Convenient monoketalization of 1,4-cyclohexanedione. Synthesis of new quinone methides
  作者：John A. Hyatt

  DOI：10.1021/jo00149a028

  日期：1983.1